Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts

Molecules

Zhili Peng¹  Maurice J. Narcis¹ 

[1] id="af1-molecules-18-09982">Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146, U

关键词: asymmetric catalysis;    nitroalkene;    Diels-Alder reaction;    helical chirality;   

DOI  :  10.3390/molecules18089982

来源: mdpi

【 摘 要 】

Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio- and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentamethylcyclopentadienes. The catalyst was found to tolerate dienes with different steric demands as well as dienes substituted with heteroatoms. The synthetic utility of 5-substituted pentamethylcyclopentadienes is rather limited, and thus we have developed a three-step route to 1,4,5,5-tetrasubstituted cyclopentadienes from commercially available ketones.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.